2-methyl-2-phenylpropan-1-amine

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-methyl-2-phenylpropylamine (7 g, 0.047 mol) and 96% formic acid (11 ml) was slowly heated to 200° C. and kept at this temperature for 1.25 hours during which time excess formic acid and water was allowed to distil. This mixture was added at 160° C. to a mixture of polyphosphoric acid (51 g) and phosphorous pentoxide (10.5 g) that had previously been heated at 170-180° C. for 1 hour. The resultant mixture was heated at 175° C. for 2 hours, before being cooled slightly and poured into water (500 ml) with stirring. The mixture was washed with ethyl acetate and the aqueous layer basified with 40% aqueous sodium hydroxide and extracted with dichloromethane (3×200 ml). Combined halogenated organics were dried (Na2SO4) and evaporated in vacuo to afford the title compound as a brown oil (5.95 g, 79%). to distil This mixture was added at 160° C. to a mixture of polyphosphoric acid (51 g) and phosphorous pentoxide (10.5 g) that had previously been heated at 170-180° C. for 1 hour The resultant mixture was heated at 175° C. for 2 hours before being cooled slightly poured into water (500 ml) The mixture was washed with ethyl acetate extracted with dichloromethane (3×200 ml) Combined halogenated organics were dried (Na2SO4) evaporated in vacuo

反応条件: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-methyl-2-phenylpropylamine (7 g, 0.047 mol) and 96% formic acid (11 ml) was slowly heated to 200° C. and kept at this temperature for 1.25 hours during which time excess formic acid and water was allowed to distil. This mixture was added at 160° C. to a mixture of polyphosphoric acid (51 g) and phosphorous pentoxide (10.5 g) that had previously been heated at 170-180° C. for 1 hour. The resultant mixture was heated at 175° C. for 2 hours, before being cooled slightly and poured into water (500 ml) with stirring. The mixture was washed with ethyl acetate and the aqueous layer basified with 40% aqueous sodium hydroxide and extracted with dichloromethane (3×200 ml). Combined halogenated organics were dried (Na2SO4) and evaporated in vacuo to afford the title compound as a brown oil (5.95 g, 79%). to distil This mixture was added at 160° C. to a mixture of polyphosphoric acid (51 g) and phosphorous pentoxide (10.5 g) that had previously been heated at 170-180° C. for 1 hour The resultant mixture was heated at 175° C. for 2 hours before being cooled slightly poured into water (500 ml) The mixture was washed with ethyl acetate extracted with dichloromethane (3×200 ml) Combined halogenated organics were dried (Na2SO4) evaporated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred suspension of lithium aluminium hydride (4.85 g, 0.128 mol) in anhydrous diethyl ether (245 ml) at ambient temperature under argon was added a solution of α,α-dimethylphenylacetonitrile (12.4 g, 0.085 mol) in anhydrous diethyl ether (105 ml) dropwise over 0.5 hour. The resultant was heated at reflux for 3 hours, cooled to ambient temperature and treated with water (4.6 ml), 15% aqueous sodium hydroxide (4.6 ml) and water (13.8 ml) dropwise sequentially. The mixture was stirred for 1.5 hours, filtered and the filtrate dried (Na2SO4) and treated with 1N hydrogen chloride in ether (100 ml). The precipitated solid was filtered and dried to afford the title compound as the hydrochloride salt (9.4 g, 52%). The resultant was heated at reflux for 3 hours filtered the filtrate dried (Na2SO4) treated with 1N hydrogen chloride in ether (100 ml) The precipitated solid was filtered dried

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred suspension of lithium aluminium hydride (4.85 g, 0.128 mol) in anhydrous diethyl ether (245 ml) at ambient temperature under argon was added a solution of α,α-dimethylphenylacetonitrile (12.4 g, 0.085 mol) in anhydrous diethyl ether (105 ml) dropwise over 0.5 hour. The resultant was heated at reflux for 3 hours, cooled to ambient temperature and treated with water (4.6 ml), 15% aqueous sodium hydroxide (4.6 ml) and water (13.8 ml) dropwise sequentially. The mixture was stirred for 1.5 hours, filtered and the filtrate dried (Na2SO4) and treated with 1N hydrogen chloride in ether (100 ml). The precipitated solid was filtered and dried to afford the title compound as the hydrochloride salt (9.4 g, 52%). The resultant was heated at reflux for 3 hours filtered the filtrate dried (Na2SO4) treated with 1N hydrogen chloride in ether (100 ml) The precipitated solid was filtered dried

反応条件: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-methyl-2-phenylpropylamine (7 g, 0.047 mol) and 96% formic acid (11 ml) was slowly heated to 200° C. and kept at this temperature for 1.25 hours during which time excess formic acid and water was allowed to distil. This mixture was added at 160° C. to a mixture of polyphosphoric acid (51 g) and phosphorous pentoxide (10.5 g) that had previously been heated at 170-180° C. for 1 hour. The resultant mixture was heated at 175° C. for 2 hours, before being cooled slightly and poured into water (500 ml) with stirring. The mixture was washed with ethyl acetate and the aqueous layer basified with 40% aqueous sodium hydroxide and extracted with dichloromethane (3×200 ml). Combined halogenated organics were dried (Na2SO4) and evaporated in vacuo to afford the title compound as a brown oil (5.95 g, 79%). to distil This mixture was added at 160° C. to a mixture of polyphosphoric acid (51 g) and phosphorous pentoxide (10.5 g) that had previously been heated at 170-180° C. for 1 hour The resultant mixture was heated at 175° C. for 2 hours before being cooled slightly poured into water (500 ml) The mixture was washed with ethyl acetate extracted with dichloromethane (3×200 ml) Combined halogenated organics were dried (Na2SO4) evaporated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred suspension of lithium aluminium hydride (4.85 g, 0.128 mol) in anhydrous diethyl ether (245 ml) at ambient temperature under argon was added a solution of α,α-dimethylphenylacetonitrile (12.4 g, 0.085 mol) in anhydrous diethyl ether (105 ml) dropwise over 0.5 hour. The resultant was heated at reflux for 3 hours, cooled to ambient temperature and treated with water (4.6 ml), 15% aqueous sodium hydroxide (4.6 ml) and water (13.8 ml) dropwise sequentially. The mixture was stirred for 1.5 hours, filtered and the filtrate dried (Na2SO4) and treated with 1N hydrogen chloride in ether (100 ml). The precipitated solid was filtered and dried to afford the title compound as the hydrochloride salt (9.4 g, 52%). The resultant was heated at reflux for 3 hours filtered the filtrate dried (Na2SO4) treated with 1N hydrogen chloride in ether (100 ml) The precipitated solid was filtered dried

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Powdered lithium aluminum hydride (137 mg, 3.61 mmol) was added portionwise to a solution of 2-methyl-2-phenylpropanenitrile (436 mg, 3.00 mmol) in tetrahydrofuran (20 mL). The resulting mixture was stirred at 80° C. overnight. The reaction was then cooled to 0° C. and water (66 μL, 3.7 mmol), 10% sodium hydroxide (1.44 g, 3.6 mmol) and water (195 μL, 10.8 mmol), respectively, were added dropwise into the reaction mixture. The suspension was filtered through anhydrous magnesium sulfate and the solution was concentrated under vacuum to give 2-methyl-2-phenylpropan-1-amine (400 mg) as a yellow oil, which was used for the next step without further purification. The reaction was then cooled to 0° C. The suspension was filtered through anhydrous magnesium sulfate the solution was concentrated under vacuum

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To an ice-cooled suspension of LAH (1.43 g, 35.7 mmol, 1.5 eq.) in dry Et2O (70.0 mL) under N2, a solution of 2-methyl-2-phenyl-propionitrile (3.46 g, 23.8 mmol, 1.0 eq.) in dry Et2O (3.0 mL) was added dropwise over 30 min. After 30 min the cooling bath was removed and the mixture was stirred at r.t. for 3 hours. The mixture was again cooled to 0° C. and carefully quenched by the dropwise addition of iPrOH (35 mL) and then 2M aq. NaOH (20 mL). The resulting suspension was filtered through celite and the filter cake was rinsed with THF. The fitrate was concentrated in vacuo. The residue was partitioned between DCM (125 mL) and 1M aq. NaOH (125 mL). The layers were separated and the aq. phase was extracted with DCM (2×50 mL). The comb. org. phases were washed with sat. aq. NaCl soln. (1×25 mL), dried over MgSO4, and concentrated in vacuo. The resulting 2-methyl-2-phenyl-propylamine was used without further purification. After 30 min the cooling bath was removed The mixture was again cooled to 0° C. carefully quenched by the dropwise addition of iPrOH (35 mL) The resulting suspension was filtered through celite the filter cake was rinsed with THF The fitrate was concentrated in vacuo The residue was partitioned between DCM (125 mL) and 1M aq. NaOH (125 mL) The layers were separated the aq. phase was extracted with DCM (2×50 mL) phases were washed with sat. aq. NaCl soln (1×25 mL), dried over MgSO4 concentrated in vacuo The resulting 2-methyl-2-phenyl-propylamine was used without further purification

反応条件: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-methyl-2-phenylpropylamine (7 g, 0.047 mol) and 96% formic acid (11 ml) was slowly heated to 200° C. and kept at this temperature for 1.25 hours during which time excess formic acid and water was allowed to distil. This mixture was added at 160° C. to a mixture of polyphosphoric acid (51 g) and phosphorous pentoxide (10.5 g) that had previously been heated at 170-180° C. for 1 hour. The resultant mixture was heated at 175° C. for 2 hours, before being cooled slightly and poured into water (500 ml) with stirring. The mixture was washed with ethyl acetate and the aqueous layer basified with 40% aqueous sodium hydroxide and extracted with dichloromethane (3×200 ml). Combined halogenated organics were dried (Na2SO4) and evaporated in vacuo to afford the title compound as a brown oil (5.95 g, 79%). to distil This mixture was added at 160° C. to a mixture of polyphosphoric acid (51 g) and phosphorous pentoxide (10.5 g) that had previously been heated at 170-180° C. for 1 hour The resultant mixture was heated at 175° C. for 2 hours before being cooled slightly poured into water (500 ml) The mixture was washed with ethyl acetate extracted with dichloromethane (3×200 ml) Combined halogenated organics were dried (Na2SO4) evaporated in vacuo